Schooner Woodwind Turns 25, Celebrates with Special Cruises

They’re some of the most recognizable sailboats on the Bay, thanks to a little movie called Wedding Crashers. And this year, the Schooner Woodwind family celebrates its 25th birthday.

The original 74-foot Woodwind began offering sailing cruises out of Annapolis back in 1993. It had seven employees. Former school teachers from Connecticut Ken and Ellen Kaye launched the business as a second career, and brought their daughter Jennifer along for the ride. She is now a co-owner and captain, and the family has added a second 74-foot schooner, Woodwind II, which appeared in the comedy Wedding Crashers, starring Owen Wilson and Vince Vaughn.

Today there are 25 employees, and the two schooners sail every day between mid-April and October. The company says it has provided sailing cruises to nearly half a million people, and a quarter of them are repeat customers.

“It’s amazing to see the families that we have been sharing our cruises with for 25 years coming back now with their children to keep this tradition of sailing on the Woodwind alive”, says Captain Jennifer Kaye.

Throughout the 2018 season, Schooner Woodwind will celebrate its 25th anniversary with special events. They include a week of unique cruises in June, including one with the boatbuilder, races between father and daughter, and special music on board. Regular sails get underway for the season on April 14.

Woodwind and Woodwind II sail from the dock at the Annapolis Waterfront Hotel located at 80 Compromise Street, Annapolis, MD 21401.  For more information, click here.